Highly-oxygenated isopimarane-type diterpenes from Orthosiphon stamineus of Indonesia and their nitric oxide inhibitory activity

Suresh Awale; Yasuhiro Tezuka; Arjun H. Banskota; I. Ketut Adnyana; Shigetoshi Kadota

doi:10.1248/cpb.51.268

Highly-oxygenated isopimarane-type diterpenes from Orthosiphon stamineus of Indonesia and their nitric oxide inhibitory activity

Suresh Awale, Yasuhiro Tezuka, Arjun H. Banskota, I. Ketut Adnyana, Shigetoshi Kadota^*

^*Corresponding author for this work

Section of Natural Products & Drug Discovery, Division of Medicinal Resources, Institute of Natural Medicine

Research output: Contribution to journal › Article › peer-review

53 Scopus citations

Abstract

From the methanolic extract of Indonesian Orthosiphon stamineus, nine new highly-oxygenated isopimarane-type diterpenes [7-O-deacetylorthosiphol B (1), 6-hydroxyorthosiphol B (2), 3-O-deacetylorthosiphol I (3), 2-O- deacetylorthosiphol J (4), siphonols A-E (5-9)] have been isolated together with nine known diterpenes [orthosiphols H (10), K (11), M (12) and N (13); staminols A (14) and B (15); neoorthosiphols A (16) and B (17); norstaminol A (18)]. Their structures were determined based on the spectroscopic data. The isolated diterpenes inhibited nitric oxide (NO) production in lipopolysaccharide (LPS)-activated macrophage-like J774.1 cells. Compounds 4-7, 9, 10, 14, and 17 showed inhibitory activities more potent (IC₅₀, 10.8-25.5 μM) than a positive control N^G-monomethyl-L-arginine (L-NMMA; IC ₅₀, 26.0 μM).

Original language	English
Pages (from-to)	268-275
Number of pages	8
Journal	Chemical and Pharmaceutical Bulletin
Volume	51
Issue number	3
DOIs	https://doi.org/10.1248/cpb.51.268
State	Published - 2003/03

Keywords

Indonesia
Isopimarane-type diterpene
Nitric oxide inhibitory activity
Orthosiphon stamineus
Staminane-type diterpene

ASJC Scopus subject areas

General Chemistry
Drug Discovery

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title = "Highly-oxygenated isopimarane-type diterpenes from Orthosiphon stamineus of Indonesia and their nitric oxide inhibitory activity",

abstract = "From the methanolic extract of Indonesian Orthosiphon stamineus, nine new highly-oxygenated isopimarane-type diterpenes [7-O-deacetylorthosiphol B (1), 6-hydroxyorthosiphol B (2), 3-O-deacetylorthosiphol I (3), 2-O- deacetylorthosiphol J (4), siphonols A-E (5-9)] have been isolated together with nine known diterpenes [orthosiphols H (10), K (11), M (12) and N (13); staminols A (14) and B (15); neoorthosiphols A (16) and B (17); norstaminol A (18)]. Their structures were determined based on the spectroscopic data. The isolated diterpenes inhibited nitric oxide (NO) production in lipopolysaccharide (LPS)-activated macrophage-like J774.1 cells. Compounds 4-7, 9, 10, 14, and 17 showed inhibitory activities more potent (IC50, 10.8-25.5 μM) than a positive control NG-monomethyl-L-arginine (L-NMMA; IC 50, 26.0 μM).",

keywords = "Indonesia, Isopimarane-type diterpene, Nitric oxide inhibitory activity, Orthosiphon stamineus, Staminane-type diterpene",

author = "Suresh Awale and Yasuhiro Tezuka and Banskota, {Arjun H.} and {Ketut Adnyana}, I. and Shigetoshi Kadota",

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AU - Awale, Suresh

AU - Tezuka, Yasuhiro

AU - Banskota, Arjun H.

AU - Ketut Adnyana, I.

AU - Kadota, Shigetoshi

PY - 2003/3

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AB - From the methanolic extract of Indonesian Orthosiphon stamineus, nine new highly-oxygenated isopimarane-type diterpenes [7-O-deacetylorthosiphol B (1), 6-hydroxyorthosiphol B (2), 3-O-deacetylorthosiphol I (3), 2-O- deacetylorthosiphol J (4), siphonols A-E (5-9)] have been isolated together with nine known diterpenes [orthosiphols H (10), K (11), M (12) and N (13); staminols A (14) and B (15); neoorthosiphols A (16) and B (17); norstaminol A (18)]. Their structures were determined based on the spectroscopic data. The isolated diterpenes inhibited nitric oxide (NO) production in lipopolysaccharide (LPS)-activated macrophage-like J774.1 cells. Compounds 4-7, 9, 10, 14, and 17 showed inhibitory activities more potent (IC50, 10.8-25.5 μM) than a positive control NG-monomethyl-L-arginine (L-NMMA; IC 50, 26.0 μM).

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Highly-oxygenated isopimarane-type diterpenes from Orthosiphon stamineus of Indonesia and their nitric oxide inhibitory activity

Abstract

Keywords

ASJC Scopus subject areas

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